Shows
Pillar Talk: Building Sales Leadership with Rick SmolenFinding Strength in Chaotic Scenarios with Bridget WinstonWe explore how a solo Camino de Santiago pilgrimage reset attention, then translate those lessons into a pragmatic playbook for fixing stalled revenue. We walk through segmentation, ICP, LTV:CAC, methodology, enablement, culture, and the myth that “it’s all talent.”• solo travel as a reset for presence and purpose• inch pebbles as a tactic for motivation and change• myth-busting the talent-first diagnosis for missed targets• clean-slate org design with segmentation by motion and support• ICP as an executive alignment tool across GTM, product, and finance• first-team mindset and Team of Teams principles• a...
2025-11-1847 minPillar Talk: Building Sales Leadership with Rick SmolenHiring Great Talent: Erich Wolters on Mindset, Clock Speed, and Closing the Deal When It CountsWe sit down with Erich Walters, VP of Enterprise Sales at Loopio, to dig into hiring for mindset over process, measuring clock speed under pressure, and making decisive calls when the quarter is on the line. We also explore AI handoffs, long-game recruiting, and why relationships still matter.• Erich’s path from Gartner mentorship to team-building philosophy• hiring great talent as the leader’s top priority• mindset versus process and how to test it• resilience, purpose and clock speed in interviews• the P-Club interview question• preparation as a filter for enterprise credibility...
2025-10-1643 minPillar Talk: Building Sales Leadership with Rick SmolenSean Munafo on Hiring Better, Building Culture, and Leading with AuthenticityWe trade super-rep heroics for scalable leadership with CRO Sean Munafo, unpacking credible swagger, the 1-3-1 framework, and how AI is splitting teams into catalysts and crutches. We share the systems, signals, and sincerity that sustain performance in hybrid work.• credible swagger as preparation, belief, and feedback loops• hiring to close your gaps, not mirror your strengths• shift from dependency to a team of leaders• remote culture: personal drivers, 1:1s as their time• escaping super-rep mode with 1-3-1 decisions• rollout that sticks: inspect what you expect• leading vs lagging indicators for...
2025-10-0844 minPillar Talk: Building Sales Leadership with Rick SmolenBeneath the Surface: Selling to Emotions, Not Just Logic with Ash KhalekSales expert Ash Khalek reveals how to identify and address the emotional factors driving buyer decisions that exist "below the waterline." His approach distinguishes between the logical elements prospects discuss openly and the personal motivations that actually move deals forward.• Pipeline coverage at quarter start often looks promising but deals stall without addressing emotional drivers• The "waterline concept" separates visible logical buying factors from hidden emotional motivations• After identifying business problems, ask "what would it mean for you personally?" then wait ten seconds• Strong rapport must be established before prospects will reveal their true personal...
2025-09-1541 min
The Supply Chaney PodcastEp. 61 - Scaling Fulfillment Operations with Rick SmolenIn this episode of the Supply Chaney podcast, Nathan Chaney interviews Rick Smolen, the Chief Revenue Officer at ShipHero. They discuss Rick's journey from a finance background to the supply chain industry, the evolution of sales in SaaS, and the role of a CRO in aligning marketing, sales, and customer success. Rick shares insights on understanding customer dynamics, ShipHero's ideal customer, and how the company is adapting to e-commerce trends. They also explore innovations in warehouse technology and the importance of community and visual content in the supply chain.Chapters00:00 Introduction to ShipHero and Rick Smolen
2025-09-0335 minPillar Talk: Building Sales Leadership with Rick SmolenThe Invisible Line Between VP and C-Suite Success with Andrea KayalAndrea Kayal, a seasoned go-to-market leader with experience as both a CMO and CRO, shares her unique perspective on bridging the gap between marketing and sales functions while making the transition to C-Suite leadership. Having worked across some of the fastest-growing B2B SaaS companies, Andrea reveals the critical mindset shifts that separate functional VPs from true C-level executives.• Appreciating the art of sales requires hiring professionals who truly understand deal management and negotiation• Using passion, curiosity, and grit as key indicators when identifying top talent during the hiring process• Shifting focus from team metrics (pipeli...
2025-09-0245 minPillar Talk: Building Sales Leadership with Rick SmolenBuilding People: How Leadership Rituals Transform Sales Performance with Colin SpecterColin Specter, SVP of Sales at Orum, shares his leadership philosophy centered on building people first, believing those people will then build successful businesses. His approach balances high standards with genuine care for team wellbeing, recognizing that sales is fundamentally about energy transference.• Zig Ziglar's principle: "You don't build businesses, you build people and people build businesses"• Leading from the front and never asking team members to do something you wouldn't do yourself• Using "Make it Happen Mondays" to begin each week with wellness practices and team alignment• Implementing box breathing exercises and other mindfuln...
2025-08-2543 minPillar Talk: Building Sales Leadership with Rick SmolenClear Expectations and Skill Capacity: A Sales Leader's Balancing Act with Chris OrlobChris Orlob, Founder and CEO of pclub.io, shares his journey from product marketing to sales leadership and discusses how to effectively develop sales teams in today's challenging environment. He offers a practical framework for setting clear expectations and explains why systematic skill development is now a strategic necessity rather than just a nice-to-have.• Chris developed his "three pillars" framework for sales leadership: managing people, managing pipeline, and managing the business• The most effective leaders make "the enemy the bar, not you" when coaching underperformers• Creating a detailed "WGLL" (What Good Looks Like) document transforms how yo...
2025-08-1845 min
The SLOBcastSLOBcast 0046 Jean Caughman Smolen. Betsy Brekenridge and Rick WrigleySLOBcast 0046 a conversation with WIS-TV Alum Jean Caughman Smolen. Betsy Brekenridge and Rick Wrigley
2025-08-1731 minPillar Talk: Building Sales Leadership with Rick SmolenCommunication is Currency: How Great Leaders Connect and Inspire with Leif O'LearyLeif O'Leary, CEO of Alegeus and veteran sales leader, shares how strong leadership skills can translate into executive success through communication, consistency, and a commitment to developing talent.Leif explains how strong sales leadership requires both consistency and positive communicationLeif emphasizes building connections with team members is essential for motivating performanceCommunication frameworks should include regular one-on-ones, steady outbound cadence, and team eventsEffective leaders understand three universal principles: people want to win, they want opportunity, and want others invested in their successThe most successful leaders genuinely care about unlocking human potential and building teamsMorning routines and consistent habits contribute...
2025-08-1152 minPillar Talk: Building Sales Leadership with Rick SmolenChecklists, Coaching, and Conversion: Sales Leadership Lessons from Wade CallisonWade Callison, CRO of Files.com, shares his journey from product leadership to sales and reveals how technical domain expertise creates credibility that transforms selling relationships from transactional to consultative.Curiosity, coachability, growth mindset, and self-awareness form Wade's core framework for identifying and developing sales talent.Wade details creating a culture of continuous learning helps sales teams adapt and improve. In one example, Wade outlines the pre-call brief that models it's thinking on the pre-flight plan that pilots benefit from.Currently focused on improving win rates at Files.com, Wade shares his strategic a...
2025-07-2150 minPillar Talk: Building Sales Leadership with Rick SmolenZen and the Art of Organizational Alignment with Thurman SneedThurman Sneed, COO of Marigold, shares leadership insights focusing on staying calm under pressure, creating organizational alignment through shared data, and building effective cross-functional relationships.Thurman tells how to stay poised during tense situations enables objective thinking and decision-makingThurman advocates for creating a "single source of truth" for data is crucial for organizational alignmentThurman emphasizes the use of regular cross-functional meetings (15-30 minutes) to build essential partnershipsThurman explains that patience is a strategic leadership quality, not a sign of complacencyWhether you're...
2025-07-1446 minPillar Talk: Building Sales Leadership with Rick SmolenBuilding Trust Across Functions with Shane EvansShane Evans, Chief Revenue Officer at Gong, brings decades of executive leadership experience to this illuminating conversation about what truly drives sales leadership success. Shane shares the frameworks and approaches that have allowed him to navigate increasingly complex leadership challenges throughout his career.Shane advocates for embracing a growth mindset and remaining open to opportunities as they arise. This philosophy has guided him through critical career transitions and ultimately to his current role at one of the most respected SaaS companies.Shane reveals his approach to joining new organizations - prioritizing relationships with c...
2025-06-2744 min
ToplineSPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of SalesWhen Rick Smolen stepped into the CRO role at ShipHero, he wasn't just inheriting a sales team—he was taking on the entire customer lifecycle. From marketing to partnerships to customer success, Rick had to quickly learn how to lead teams in functions he'd never directly owned before. In this episode, he shares what that transition was really like, the mistakes he made early on, and how curiosity became his most powerful leadership tool. You're invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going be...
2025-05-0826 minPillar Talk: Building Sales Leadership with Rick SmolenEndurance and Optimism in Sales Leadership with Justin GriffinIn this episode of "Pillar Talk," Rick Smolen chats with Justin Griffin, SVP of Sales at Computacenter, exploring the resilience required in sales leadership, the journey from individual contributor to leader, and the delicate balance between professional and personal success.Episode Highlights:Justin Griffin shares his experience dealing with the demanding schedule of a sales leader and balancing multiple priorities.Discussion on the transition from an individual sales role to leadership, highlighting the natural movement into management as individual success accelerates.Insights into the importance of endurance, optimism, and a positive mindset in navigating...
2024-05-1743 minPillar Talk: Building Sales Leadership with Rick SmolenThe Evolution of a Sales Leader with Ed McDonnellThe Pillars of Sales Leadership with Ed McDonnellIn this enlightening episode of Pillar Talk, Rick Smolen dives into the intricacies of sales leadership with the remarkable Ed McDonnell, the current CRO of Asana. With a friendship and professional relationship spanning over two decades, Rick and Ed explore Ed's impressive journey from his early days at Thomson Financial to leading organizations at Salesforce.com, and now as CRO at Asana. This conversation sheds light on the behaviors, actions, and strategic pillars that underpin successful sales leadership, providing valuable insights for current and aspiring leaders in...
2024-05-0344 minPillar Talk: Building Sales Leadership with Rick SmolenBuilding a Sales Leadership Legacy with Jonathan PollackIn this episode, Rick Smolen chats with Jonathan Pollack about his journey from an individual contributor to a leader in sales at companies like Intralinks, Shibumi, and Augury. They discuss the nuances of building a strong sales team, fostering a positive work culture, and maintaining team motivation in remote settings.Key Points:Career Growth: Jonathan's progression from hands-on sales roles to senior leadership positions, emphasizing the lessons learned and strategies implemented along the way.Leadership and Culture: Insights into creating a team culture that motivates and excels, even under minimal...
2024-04-1545 minPillar Talk: Building Sales Leadership with Rick SmolenMastering the Craft of Sales Coaching with Brian WalshWelcome to another episode of Pillar Talk, where we delve deep into the foundations of sales leadership success. In this episode, we're honored to have Brian Walsh from Force Management join us to share invaluable insights into the art and science of sales coaching.Key Takeaways: Behavioral Influence of Senior Leadership: Senior leaders set the tone for the organization's coaching culture through their actions and priorities.Importance of Coaching Coaches: Coaching at the managerial level is pivotal for consistent and impactful skill development across the sales team.
2024-04-0545 minPillar Talk: Building Sales Leadership with Rick SmolenMastering Coaching with Dave KennettIn this episode of Pillar Talk, Rick Smolen is joined by Dave Kennett, the founder and CEO of ReplayzIQ, a pioneering sales call intelligence platform. With a rich background in sales leadership and a profound emphasis on coaching, Dave shares his extensive experience and invaluable lessons on building a robust coaching culture within sales teams.Key Highlights:Journey to Sales Coaching: Dave recounts his early career at WW Granger, where a significant investment in sales training led to pivotal insights on the importance of integrating learned skills into a company's fabric, sparking his l...
2024-03-1539 minPillar Talk: Building Sales Leadership with Rick SmolenThe Growth Framework that drove a successful IPO with Dan HeadWelcome to another episode of Pillar Talk with Rick Smolen, where we dive deep into the realms of sales leadership and uncover the strategies that define success. This episode features Dan Head, the accomplished CEO of Phrasee, sharing his insights that guided from from a seasoned sales leader to CRO, and now CEO.About Our Guest:Dan Head has an impressive career trajectory, evolving from senior sales roles at giants like Salesforce and Infor to leading AppBoy through its transformation into Braze and its subsequent IPO triumph. Key Discussion P...
2024-03-0848 minPillar Talk: Building Sales Leadership with Rick SmolenMastering Market Dynamics with Sam JacobsWelcome to this episode of the Pillar Talk Podcast, where we delve into the intricacies of sales strategies, business planning, and the importance of P&L fluency with our guest, Sam Jacobs, the CEO of Pavilion. Discover invaluable insights on navigating high-growth environments, the pitfalls of revenue-driven models, and the transformative power of understanding unit economics.Key Highlights:The Art of Business Planning:Explore the strategic importance of proactive business planning.Understand the challenges and solutions for staying ahead in high-growth scenarios.P&L Fluency: Essential for Modern Sales L...
2024-03-0140 minPillar Talk: Building Sales Leadership with Rick SmolenNavigating Sales Leadership with Kyle NortonIn this episode of Pillar Talk, Rick Smolen chats with Kyle Norton, the CRO of owner.com, to explore operating rhythms in sales leadership. Kyle, with his rich background in sales leadership roles across companies like Shopify, League, and now Owner.com, delves into how establishing a robust operating rhythm is crucial for sales teams to achieve targets today and in the future. The discussion navigates through Kyle's personal journey and lessons learned, highlighting the importance of forward planning, the critical role of headcount planning, and the necessity of building a bench for future growth.
2024-02-2345 minPillar Talk: Building Sales Leadership with Rick SmolenBuilding a High-Performing Sales Team with Mark KosoglowWelcome to Pillar Talk, where we dive into the foundations of sales leadership success. In this episode, we're thrilled to have Mark Kosoglow, a renowned figure in sales leadership, share his wealth of knowledge and experience. Mark delves into the intricacies of hiring a high-performing sales team, focusing on talent identification, innovative interviewing techniques, and fostering a culture of success.Highlights:Introduction and Background Rick introduces the podcast theme and guest Mark Kosoglow, touching on Mark's impressive background and contributions to the sales community.Talent Identification and Attraction Mark di...
2024-02-1636 minPillar Talk: Building Sales Leadership with Rick SmolenConnecting Sales Process, Negotiation, & Forecasting together with Brian McDowellIn this edition of "Pillar Talk," Rick Smolen converses with Brian McDowell about instilling consistent sales process, adherence, and customer verifiable outcomes connected to forecasting. With his rich experience in sales, including his role as CRO, Brian shares invaluable insights on enhancing sales processes and team dynamics.Key Topics Discussed:Revisiting Sales Leadership Roles: Brian reflects on the transition from an individual contributor to a sales leader, focusing on coaching and guiding teams through challenging parts of the sales process.Implementing Effective Sales Processes: The episode delves into strategies for establishing structured sales processes, including the...
2024-02-0935 minPillar Talk: Building Sales Leadership with Rick SmolenMastering Communication in Sales Leadership with Christina BradyIn this insightful episode of "Pillar Talk," Rick Smolen engages with Christina Brady in a deep dive into the essential role of communication in sales leadership. Christina, with her extensive background in sales leadership and unique experience as an artist and musician, brings a fresh perspective on how effective communication can drive success in sales teams.Key Topics Discussed:The Pillars of Sales Leadership: Rick outlines the show's focus areas, emphasizing hiring, operating rhythm, business planning, mastering the craft, communication, and ownership.Communication as a Key Pillar: Christina highlights communication as a crucial element for success...
2024-02-0236 minPillar Talk: Building Sales Leadership with Rick SmolenWelcome to Pillar Talk: Building Sales Leadership with Rick SmolenJoin Rick Smolen and other seasoned B2B sales leaders on the quest for defining great sales leadership. Learn the pillars of successful leadership, hear stories about what works and what doesn’t, learn lessons, and come away with specific tactics you can apply to your job or career.Music by Ben Cina & Ayler Young
2024-01-2505 min
Voyage of RediscoveryVoyage of Rediscovery - Conversation with Rick SmolenThis episode of Voyage of Rediscovery features Richard (Rick) Smolen.
Rick attended Penn State University, and is originally from the Yardley, Pennsylvania area, just outside of Philadelphia.
A successful sales leader, Rick shares how selling ads eventually led him to Semester at Sea. He also tells us about his time in Vietnam, and the tastiest, most satisfying gelato he's ever had.
Hop on board everyone, the ship is leaving.
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About the Voyage of Rediscovery
Voyage of Rediscovery commemorates the 25th anniversary of the Fall 1998 journey of Semester a...
2023-10-0826 min
The GTMnow PodcastGTM 19: The Art of Sales Leadership with Rick SmolenIn this episode, we are joined by Rick Smolen. Rick is the current Head of Sales at Loopio. He is a results-focused revenue leader with over 20 years of experience in tech and enterprise software sales. Rick used to be the Head of Sales at Greenhouse Software, where he oversaw the company's annual recurring revenue tripling to over $65 million in less than three years. Prior to that, he spent over a decade at Interlinks in sales, sales leadership, and international roles, and helped the company grow to over $300 million in annual sales.What You Will Learn:
2023-01-2443 min
Bowery Capital Startup Sales PodcastWhy Your Sales Capacity Plan Doesn't Work with Rick Smolen (Intralinks)Rick Smolen, Former VP of Sales at Intralinks and Greenhouse, joins the Bowery Capital Startup Sales Podcast to discuss "Why Your Sales Capacity Plan Doesn't Work".
2020-03-1626 min
What's Your Work Fit?Give Piece a Chance Part 2Give Piece a Chance Part 2: An Entrepreneur Disrupts Chicago’s Food Scene
About this episode:
“We didn’t have the luxury of a soft opening. So, we’re packed, it’s hard getting the product out of the kitchen, because we really don’t know how to do volume yet. And we’re learning how to do service. So, we’re pissing off people right and left and it took awhile to settle down. And fortunately, it did. But definitely it was a double-edged sword. And we were in the papers; we were in the media all of the t...
2019-10-1131 min
The GTMnow Podcast5. Moving Your Product (And Your Sales Team) Upmarket w/ Rick SmolenOn this episode of the Sales Hacker podcast, we talk with Rick Smolen, VP of Sales at Greenhouse about moving your product upmarket and how to sell your software to a big company. The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
2018-05-0142 min
The Sales Hacker Podcast5. Moving Your Product (And Your Sales Team) Upmarket w/ Rick SmolenOn this episode of the Sales Hacker podcast, we talk with Rick Smolen, VP of Sales at Greenhouse about moving your product upmarket and how to sell your software to a big company.
2018-05-0142 minThe Sales Hacker Podcast5. Moving Your Product (And Your Sales Team) Upmarket w/ Rick SmolenOn this episode of the Sales Hacker podcast, we talk with Rick Smolen, VP of Sales at Greenhouse about moving your product upmarket and how to sell your software to a big company.
2018-05-0142 min